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Org Lett. 2016 Oct 07;18(19):4990-4993. doi: 10.1021/acs.orglett.6b02454. Epub 2016 Sep 27.

Rh(II)-Catalyzed Transannulation of N-Sulfonyl-1,2,3-Triazoles with 2,1-Benzisoxazoles or 1,2-Benzisoxazoles.

Organic letters

Xiaoqiang Lei, Mohan Gao, Yefeng Tang

Affiliations

  1. School of Pharmaceutical Sciences, Tsinghua University , Beijing 100084, China.
  2. Collaborative Innovation Center for Biotherapy, State Key Laboratory of Biotherapy and Cancer Center, West China Medical School, Sichuan University , Chengdu 610041, China.
  3. Beijing National Laboratory for Molecular Sciences (BNLMS) , Beijing 100190, China.

PMID: 27672715 DOI: 10.1021/acs.orglett.6b02454

Abstract

A Rh(II)-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles with 2,1-benzisoxazoles has been developed, which affords an efficient method for the synthesis of quinazoline derivatives. The transformation represents an unprecedented example which utilizes N-sulfonyl-1,2,3-triazole as an aza-[2C]-component in cycloadditions. Meanwhile, a Rh(II)-catalyzed formal [3 + 2] cycloaddition of N-sulfonyl-1,2,3-triazoles with 1,2-benzisoxazoles is also presented, which enables the rapid synthesis of functionalized imidazole derivatives.

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